Deanna Winchester
by Voldivoice
Summary: : Dean was born Deanna, and this changes the relationship between her and Castiel! We start from Season 5 episode 3 and it may be Castiel's last night on earth! AU Genderswap.
1. Chapter 1

**Disclaimer: I don't own Supernatural. **

**Author's Note: Dean was born a woman, Deanna, and although their personalities are not entirely different, it changes her relationship with a certain Angel. Deanna isn't strictly heterosexual, so she's had homosexual hook-ups, such as with Lisa, but of course there would have been no chance she was Ben's father lol. I know gender swap has probably been done before, but I wanted to try my hand at it! But this story will focus on Deanna and Castiel. We start in Episode 3 of Season 5, Sam and Deanna have gone their separate ways, and Castiel contacts Deanna for help in finding the Archangel Raphael! I imagine female Dean as Katee Sackhoff from BSG. For now there will be a lot of similarity with the series, so it may look like I'm just copying out the episode word for word, but It will get more individual and distinctive after this chapter, this is a What If? scenario after all!**

Chapter 1: A Mission of Mercy

Deanna Winchester knocked back her whiskey in one shot, wincing slightly at the burn. She received drunken hoots and clapping from the surrounding men, bikers and malcontents, who were getting off on watching a babe and a Hells Angel having a drinking contest. She slammed the glass rim down onto the bar table, next to the other 15, and linked her hands above her head in a stretch, smirking at the greying, leather clad man opposite her. He stared at her grimly, reaching a calloused hand to the table and dragging the glass towards him, the rim scraping on the table. He downed the drink methodically, grunting as he slammed the glass down, determined not to be bested by a woman, but Deanna could see the tremor ricochet up his arm, making him sway slightly. Taking the initiative, Deanna reached her hiking boot clad foot under the table, connected with her opponents chair and pushed. As predicted, the chair toppled over, biker with it, and he was too drunk to stand up. He remained a crumpled heap on the floor, despite the pleas and shouts of his cohorts.

"Guess that means I win guys, pay up!"

The bikers grumbled, handing over the money as Deanna hung lazily in her chair, smirking and making wise cracks.

"Thank you, thank you, I'll be here all week. Try the veal!"

Deanna shirked on her brown leather jacket, pulling her long layered blond hair out from the collar, and gleefully gathered up the notes that had been slammed on the table. Without counting she knew it had to be close to $600, no credit card fraud necessary for a few days. She took a $50 out and handed it to the bartender, a good looking Hispanic guy named Juan who she'd flirted with a little. She told him to keep the change and swaggered her way out of the bar, missing his look of disappointment, he had hoped she'd wait until his shift ended. Deanna didn't feel like hooking up tonight, but drinking was her way of celebrating a successful vampire hunt, especially without bitch-face looking at her disapprovingly.

Deanna walked across the empty road, into her motel room, and collapsed on her bed, face first, she didn't wake up until dark the next day.

Deanna woke up with a dry taste in her mouth, and dragged her numb limbs out of the bed, shirking off her clothes and walking naked into the shower. She supposed there was one perk to not having Sam here, clothing optional days. She turned the water to almost boiling, washing herself and her hair with the motel soap. One of these days she'd have to buy some shampoo, or get a haircut. Personal grooming hadn't been top priority since the apocalypse started, hell, even before that she hadn't cut her hair since she woke up in her own grave. Thinking of this Deanna looked at her arm, which still sported a human hand print, although nowhere near as prominent as it had been then, there was still shiny scar tissue where Castiel's hand had "raised her from perdition". The little dweeb had a fancy way of saying "pulled you out of hell", but Deanna had to admit the dork-angel had his cute moments.

Deanna turned off the water and stepped out of the shower cubicle, feeling the chill of the air on her skin she grabbed a towel and dried off before pulling on some clean underwear. She only had the lacy stuff left; she needed to do some laundry soon. She'd nabbed this Victoria Secret number from a Laundromat, it had fit so she kept them, but they weren't really her speed. She walked to the mirror, with her hairbrush, raking it through her hair and glancing at the anti-possession tattoo on her hip. It didn't look new anymore, already starting to get the faded look of a veteran tat, it was the first thing she'd had redone when she'd been resurrected. She'd woken up brand new, a virgin in _every way_, and she still hadn't fixed that, been a bit too busy saving the world, or at least, marginally keeping the inevitable at bay. She threw the brush behind her onto the floor and reached down for the complimentary mouth wash, looking into the mirror to get the fright of her life, Castiel was standing not 3 inches behind her, looking at her with innocent interest.

"Don't do that!"

"Hello Deanna"

Deanna turned around and was suddenly aware that she was in sexy underwear in a motel room with an angel standing in front of her. Castiel was intently looking at her face, he hadn't noticed her state of dress yet.

"Cas, we've talked about this, personal space!"

"My apologies"

Cas stepped back and seemed to suddenly realise that crucial pieces of clothing were missing, he began to blush. So Angel's blushed, huh. Deanna edged away from the sink, walking away from Cas to where her clothes were, she suddenly felt vulnerable, which was quite out of character, and wanted to cover up. She told herself it was for Cas's sake, who was now actively avoiding looking at her. He'd probably never seen a chick without clothes on before.

"How'd you find me? I thought I was flying below the Angel-radar"

Deanna pulled on a clean tank top and yesterdays jeans. She still felt quite exposed, so grabbed a plaid shirt too.

"You are, Bobby told me where you were."

Deanna adjusted the shirt, pulling her hair out of the collar, watching Castiel examining the room, looking for something. He saw she was clothed and now his eyes stayed trained onto her. He was always with the intense staring.

"Where is Sam?"

Deanna felt something pull at her heart, making it heavy, she didn't want to talk about her failure with Sam. She tried a diversionary tactic.

"Me and Sam have taken separate vacations for a while. So, did you find God yet? More importantly can I have my damn necklace back please?"

"No, I haven't found him, it's why I'm here..."

Cas, then proceeded to tell Deanna of his plan to catch a Teenage Mutant Ninja Archangel in order to interrogate him to find where his Dead-beat Dad was. Deanna was very sceptical of this plan, but the serious look on Cas's face was quite endearing, as usual, she resorted to sarcasm.

"So what? I'm Thelma and you're Louise and we're just going hold hands and sail off this cliff together?"

Cas had looked blankly at her, as usual. She really needed to get him to watch some TV, it'd do the guy some good. Deanna replied with another comment, turning round to find her face was less than an inch away from Cas's, his blue eyes stared into her own, and his head was tilted to one side.

"I need your help, because you are the only one who'll help me. Please."

Cas's stare was doing something to her insides that she didn't think was strictly Angel-kosher. Well, she didn't have any other plans tonight.

"Fine, it's a date, but you better not try anything funny, my brother has a shot gun."

"Why would Sam's possession of a weapon be pertinent in this case? Archangels are not affected by bullets."

Deanna rolled her eyes, and didn't bother trying to explain.

"Where is this Raphael?"

"Main, let's go." Cas reached out with his fingers together to transport them.

"Woah, last time you zapped me someplace I didn't poop for a week, we're driving."

Deanna grabbed her boots and gear and left the motel, a puzzled but pleased angel trailing behind her like a lamb.

...

They stopped at a McDonalds on the way, to let Deanna change into something more FBI friendly. Deanna hated the skirt suit, but the macho types felt more comfortable talking to a woman in a skirt, it made her seem less intimidating, she and Sam had liked to play good cop bad cop. Sam...she wouldn't think about it. She'd put some make-up on and pulled her hair back into a professional bun. Her heels pinched, she needed to invest in better footwear. Cas had stared at her when she came out.

"Deanna, you are wearing a skirt."

"No shit Sherlock."

"You look...very female."

That was an odd response from a guy who'd seen her underwear last night, but then, Castiel was odder than Willy Wonka.

"I was last time I checked. Thanks Casanova, let's go."

"My name is not Casanova, it is Castiel. Who is this Casanova you speak of?"

"I'll tell you when you're older."

"Also, how is the children's box meal meant to deliver happiness?"

Deanna could tell this police interview was going to be fun.

...

Castiel's attempts to act like a FBI official had been lacklustre at best; at least he had looked the part, but that was really due to Jimmy Novak, "Holy Tax Accountant" she'd called him once, but the office wear seemed like skin to the angel. Castiel without the suit and coat was like Superman without tights. At least they knew where to find Raphael's vessel now, they'd stake the place out tomorrow. After their interview Cas had disappeared, sometimes the guy was like freaking Batman. Not knowing when he'd show up again, Deanna went to the local D.I.Y store to grab some supplies, ate, and then went back to her base in the abandoned house she and Cas had broken into. She was glad she'd showered yesterday; the water in this place was brown. A few hours later, once it was dark and Deanna was sick of researching, Cas reappeared with a weird vase.

"Where have you been?"

Great, now she sounded like an angry house wife.

"Jerusalem."

"Oh, how was it?

"Arid."

Castiel walked over to the desk she'd just put her book on, he placed the vase on it. It looked hand-made and old, definitely not Pottery-Barn.

"What's that?"

"Oil, it's very special and very rare."

Cas looked distracted, his eyes shifty as he sat down in the chair, their conversation turned more serious as he described the difficulty of trapping Raphael in order to question him.

"Do we have any chance of surviving this?"

Castiel nodded towards her with his head.

"_You _do."

Deanna walked from in front of Cas to behind him, she couldn't look him right in the eye at the moment.

"So odds are you're a dead man tomorrow."

"Yes."

Cas said this with such calm and finality it stunned her. Deanna knew what is was like to die, and what Raphael would do to Cas was probably only a fraction of what those Hell hounds had done to her, never mind the 40 years of hell afterwards. Thinking of that time with Alistair, his slimy hands on her, the knives, the weapons, cutting into her, Deanna really needed a drink. Deanna covered her pause with joviality.

"Wow, so last night on earth, any plans?"

"I just thought I'd sit here quietly."

Was Cas being serious? This guy needed to get a life, but at the same time it was a little sad. Deanna stood behind Cas, who was sitting in the chair, and suddenly felt the need to stir him into action. How could he just sit there and wait for the end?

"Oh come on, anything? Booze? Women?"

Cas's head turned round and his eyes flickered involuntarily to Deanna's breasts, then up to her eyes, and back and then he moved his head away, flustered. Deanna began to suspect something.

"You have been with a woman before? Right? Or an Angel at least?"

Cas looked even more wide eyed and frantic, twitching he unconsciously rubbed at his neck.

"You mean you haven't been up there pushing the clouds? Ever..?"

Cas went on the defensive now, attitude inserted into his speech, Deanna had taught him well:

"I haven't has occasion, _okay_."

Poor guy, possibly dead as disco tomorrow and had never been laid, it sounded like a bad pick up line. He just looked so small, innocent and pathetic sitting there in the dark. It was a sad state of affairs when the only person in the entire world Cas could ask for help was her. For a second Deanna considered taking him out, finding him a professional, but if he was this freaked out with just her, what would he be like in public with a hooker? Deanna made a decision.

"Alright, there are two things I know for certain" she said as she shirked off her plaid shirt:

"1. Bert and Ernie are gay and 2. You are not going to die a virgin on my watch, come on."

Deanna grabbed Castiel's hand but he remained seated, he looked petrified.

"Where are we going?"

"Upstairs"

"Why?"

Cas's eyes were wide and frantic, his Adam's apple prominent as he swallowed, for a fraction of a second Deanna found it funny an Angel had an Adam's apple.

"Well Cas, there's a fairly decent bed upstairs and we're alone. When you resurrected me, you made me brand spanking new, which included the one thing a woman's _never_ supposed to get back. Seeing as you might kick the bucket tomorrow and I don't feel like being "The Virgin Goddess Deanna" anymore, which _is_ technically you fault, we're going to be friends and help each other out."

"What are you saying?"

"We're having sex genius."

Cas looked like a deer in headlights, pale and wide-eyed as Deanna yanked him from his chair and started leading him upstairs. It was for his own good, and she tried to convince herself she hadn't thought about doing it before.

This was a mission of mercy, Cas needed to be relieved of his V card. Who else could she trust to do it right?

...

**Author's Note: Please Read and Review!**


	2. Chapter 2

**Disclaimer: I don't own Supernatural. **

**Author's Note: Here's the close encounter, thanks for your reviews! I've made a point not to be overly explicit because of the guidelines!**

Chapter 2: You rocked me all night long

Castiel sat on the double bed, hands on his knees as they jiggled about nervously, face white and eyes wide.

"Fornication is a sin Deanna."

Deanna was by her duffle, taking out her sleeping mat and bag, and nodding her head for Castiel to move, he jumped quick as lightning off of the bed as she unzipped the bag and laid it out flat, making a blanket covering for the bed.

"So are coveting, wrath and gluttony and I do a whole lot of that too."

Castiel stayed in the corner, eyes intent on Deanna's every movement, as if at any moment she would attack. Deanna felt like rolling her eyes as she pulled out her portable ipod speakers and set up her "Smooth tunes" playlist. "In a Gadda da Vida" began playing, and Deanna almost felt like laughing. Sam had bitched about her tapes for so long, she'd updated to a friggin' ipod, but kept the same music.

Thinking about Sam would not bring on the right mood.

Music was done, the playlist lasted around 3 hours, definitely enough time to ruffle an angels feathers.

The only light was from the moon; Deanna hadn't wanted to attract attention by connecting the electricity. Deanna pulled out a candle from her bag, and used her pen knife to cut it into three pieces and put them in three different parts of the room. The flickering light set the "mood", this was one of the things Deanna had learned from Lisa. Lisa had liked fragrant candles and hippy music, but she could set a hell of an atmosphere. She'd been into that tantric stuff, the anticipation and foreplay, which was cool in itself, but Deanna had always been a "straight to the point" gal. But maybe, in Cas's case, he needed to be broken in easy.

Castiel moved cautiously out from the corner, keeping his back to the wall, and approached the candle next to the bed, as if drawn to it. It seemed to relax him a little, looking into the light, so Deanna left him there for a while as she grabbed some tic tacs. She shoved three into her mouth and then tested her breath, Minty fresh. Glancing over at Cas she walked over and took his hand.

"Chew this, you'll like it"

Castiel looked at the tic tacs bewildered but shoved them into his mouth and chewed, his eyes widened at the flavour. It seemed to distract him from the situation.

While he chewed and stared at the candle Deanna took a bottle of water and walked out of the room into the ensuite, sitting on the rim of the grimy bath and taking off her boots and socks. She pulled off her jeans and poured the bottle of water on her feet, rinsing them off, before wetting her jeans and wiping off her face and arms.

Deanna had the sudden urge to examine herself and wiped off the dusty mirror, her hair was awry, so she flattened it down, and she examined herself from the front and the side. She'd do.

Time to put her game face on, she didn't know why she was screwing around. Deanna gave herself a shake and straightened her shoulders, before walking into the bedroom with confidence.

"Wild Horses" had begun to play and Cas was still standing stock still by the candle, Deanna walked over and touched his shoulder, he allowed himself to be turned round and took hold of his tie, gently leading him back to the bed. Deanna stopped at the foot of it, and Castiel looked discomforted again.

"Cas, you know you can say you don't want to, "Just Say No" and all that."

Cas contemplated her face, which without her boots was two inches lower than usual, and said.

"I admit I am apprehensive, but you are my friend Deanna, and you have never betrayed my trust."

"I take it that's a "yes" then?"

Castiel looked her in the eyes and nodded, he looked so serious it almost made Deanna laugh, but the way the eyes pierced her did something unusual to her insides.

"Alright then, let's get this show on the road."

Deanna ran her hands down the lapels of Castiel's beige coat, slipping her hands inside and sliding it down his shoulders. He stood perfectly still as it dropped slowly down his arms, revealing the suit underneath. For some reason, de-clothing Cas felt really intimate, more so than with anyone else, maybe because she knew him so well, she was usually a hook-up person. Castiel's eyes watched as she did the same for his suit jacket, revealing the crisp white shirt underneath, it felt like removing his armour. Then came his tie, she undid the knot, aware of her close proximity to his face, his breath upon her nose, as she slowly drew it from around his neck, letting it slip from her hand to the floor.

"Cas, this isn't a spectator sport."

"Am I not performing correctly?"

Deanna sighed and took Cas's hand, putting it on her waist.

"Just do what comes naturally, and if it doesn't, I'm sure Jimmy knows what to do."

For a moment Deanna was slightly weirded out by the thought that technically she would be having sex with Jimmy, but Cas was the one awake inside of him, she puzzled over that for a minute. But Cas moved his hand from her waist, trailing it up her arm until he reached her hair, trailing it through his fingers.

"I like that you let it grow, when I rescued you from Hell your hair was decidedly masculine."

"Thanks Cas, that was kind of poetic."

"Today, in the suit, your skirt, I liked that too. You are a very well proportioned female, with a pair of attractive legs."

Where was Cas getting this from? Was he a leg man? Deanna glanced down at her bare legs, she'd taken her jeans off in the bathroom, all she had on were the Victoria secret panties.

Castiel slid his hand from her hair, down her arm and came to rest on the top of her bare leg.

Castiel's eyes were inquisitive and slightly hooded, his voice became deeper, almost a whisper as he said:

"Am I doing this correctly?"

If Deanna didn't know better she would have sworn he'd done this before, he was definitely working on her. It was time to take the initiative back, who was teaching who here?

"You get a gold star Cas" she said, as she began to undo the buttons of his white shirt, slowly, and one at a time. Finally, it was open and she reached skin, which radiated a comforting warmth. She slid the shirt off and Cas's skin was revealed to her, smooth and pale, and a nicely defined body.

"You've been holding out on me Cas, you're buff under all those clothes."

"Jimmy Novak took regular trips to his local Gym, he considered his body a temple for God. He was surprised to learn of his accuracy."

"Well thank you Jimmy."

A thought occurred to Deanna.

"Is he cool with this?"

"Jimmy Novak understands that my actions and his are separate. While I inhabit his body he is in hibernation, and does not object or participate."

"Thrusters on full then, Captain."

"I was the equivalent to a Captain in my garrison, so I suppose your analogy is accurate. However, I do not possess thrusters."

Deanna cocked her eyebrow and a smirk came on her face, Cas would always say the most funny shit without even realising it. She liked that about him, he was straightforward and honest.

"Captain Cas, take off my shirt."

Castiel's hand moved from her hip to the hem of her tank top, sliding under to find her belly button and then reaching to lift it. He saw her anti-possession tattoo and said.

"While your ward is effective, if I inscribed it onto your bone it would be less likely to fade or become broken with time."

"I think you've signed your name enough on my skeleton, but thanks Cas."

"How did you know I left my signature?"

Deanna looked up to see a slight smile on Cas's face, so he was a wise guy eh?

"Oh you're just freakin' hilarious Cas."

Castiel cocked his head before lifting up Deanna's shirt, waiting for her to lift her arms, he let it drop to the side in a mechanical motion that mimicked Deanna's own sloppy movements of earlier. Now Deanna was in her underwear and Cas in his trousers and shoes. Deanna needed to even the playing field, was Cas a briefs of boxers Angel?

Deanna put her hands on his shoulders and gently pushed, he sat down on the edge. He seemed to have gotten the hang of this because he kicked off his own shoes while Deanna reached for his belt. With a practiced motion that cause Castiel to cock his head, Deanna slid the belt out from its loops fluidly, letting it fall to the side.

Deanna stood in front of Castiel in only her underwear, while he sat with his suit trousers on, they stayed like that for an age, just watching each other before one of them made the first move, surprisingly, it wasn't Deanna. Castiel reached forward and took Deanna's waist, pulling her towards him, her knees hit the edge and bent, and suddenly she was straddling him.

"Where'd you learn that?"

"I saw it on television."

"What were you watching?"

"I'm not aware, but there were Doctor's who were having a lot of intercourse, disproportionally to the amount of healing they performed, and the leader was wearing cow boy boots."

"Dude, you were watching Doctor Sexy MD, I lov...I watch it occasionally, when I'm channel surfing."

"The title seems very accurate. It was compelling."

Deanna and Castiel were now face to face, barely inches away, and seemingly hypnotised by one another, until Castiel broke the trance by leaning forward and kissing her furiously.

After a few minutes, they broke apart, Deanna felt out of breath, but Castiel seemed unaffected. Yet, his eyes appeared darker.

"You got that from watching Doctor Sexy MD? And they say TV isn't educational."

Deanna reached down and undid the button on his trousers, then slowly slid down the zip, now Cas looked a little stiff again. So he was a boxers guy. Deanna moved off of him and nudged him to move backwards up the bed, suddenly the clothes were gone and they were both in their underwear. Deanna crawled back onto the bed to Cas, who was sitting by the headboard, having lost some of the confidence he had derived from his TV recollections.

"Still want to do this?"

Castiel swallowed hard, then nodded as Deanna straddled him, taking charge.

They were kissing again, then touching, Deanna's movements deft and confident while Castiel's were hesitant and light. They explored, hands running through hair and on skin, skimming underwear and moving underneath it. All of a sudden Deanna's bra was gone, and she encouraged Cas to explore that area. The petting became more frantic, kisses longer and deeper, breathing harder, hands finding cloth and removing it, until they were as bare as Adam and Eve.

The candles flickered, shadowing their tangled limbs against the faded wallpaper. The female shape move over the male and then they were joined.

Castiel stared up at Deanna as if he had received a revelation, Deanna remained still, feeling the sting, she hadn't remembered how uncomfortable it had been the first time, but then she had been 16. Cas seemed to sense her discomfort, he reached his hand up and cupped her face bringing it down to his own, and then they were kissing again, touching and after a minute, they were moving.

In the grand scheme of things, it hadn't lasted long, under different circumstances Deanna would have laughed her ass off at a guy for lasting only 3 minutes. But this was different, this was Cas, she watched as he turned from a timid boy into a man beneath her, participating, anticipating, eager and finally, bordering on confident. Towards the end, he had flipped them over, and suddenly he was on top, he was setting the time, he was in charge and then they had held each other as they shook. Deanna found that she didn't mind Cas being on top, while she hated being bottom with most guys, with Cas it was different, the whole thing had been different.

Deanna had never been one to snuggle with a guy, she'd never felt comfortable enough, connected enough to stay a whole night. Not that she didn't want to snuggle sometimes, but she didn't want to appear pathetic, whimpy, damn stereotypically girly, for doing so. She'd indulged with Lisa, but it was different with a woman, she hadn't felt as pressured into a role. When in relationships she felt she had to be the butch, take charge, lead the way and then leave, Guys could be surprisingly clingy.

The life of a hunter was hard, and it changed you from the ground up, if you got attached to something, or someone, it was bound to be taken from you. She hadn't wanted to get too close, become a broken shell like her father after their mother was murdered. But this was Cas's last night on earth, most likely, no time to get attached, no chance of repetition, and he was her best friend, so when Cas reached for her, she let him, and they lay facing each other, faces inches apart, and arms around each other.

Deanna finally noticed the music again, as her skin began to cool, "I'm loving Angel's instead" was playing, she hadn't put that on her playlist, who... Sammy, he must have been screwing with her music again. God was definitely a sadist. Cas may die tomorrow, would he go back to heaven? To the _welcoming_ arms of his siblings? Or be sent to hell? Would he go anywhere?

Suddenly Cas's face changed from a lazy smile to a grin and he said:

"I see now why Sam would need a shotgun, to fend off wayward males wishing to copulate with his sister."

Something inside Deanna snapped and suddenly she was laughing so hard it hurt, holding her sides and almost rolling on the bed, with Cas smiling bemused at her.

"Oh...I haven't laughed like that in years."

"Was what I said particularly amusing?"

"Ah Cas, you have no idea."

The air began to chill and Deanna shifted, grabbing her tank top and pulling it on, but unable to locate her panties, she gave up and flopped back onto the bed beside Cas with a beer from the portable cooler, Cas had followed her lead and pulled his boxers back on.

"Deanna, I find I have far more vested interest in my survival tomorrow."

"Yeah" Deanna said as she offered him the beer and he sniffed it before handing it back, "Why's that?"

"I don't want tonight to be the only night I experience copulation. I find it to be a far more rewarding experience than I anticipated."

Deanna smirked.

"That your way of saying I'm a good lay Cas? Can't say I've had a guy want to keep on living by sleeping with me before."

"You and I share a profound bond, I raised you from perdition, and you have trusted me and aided me countless times, at your own bodily and mental detriment. This physical experience has deepened out spiritual connection."

Cas reached out and placed his palm precisely on her resurrection scar, where his hand had marked her for life.

Suddenly, Deanna knew that if they survived tomorrow, things were going to get far more complicated.

Crap.

"Deanna, would you be opposed to my initiating intercourse again? I've heard it is an experience enriched through repetition."

"Sure Cas, I've got some moves I can show you, my padawan."

"What's a padawan?"

Deanna shut him up by kissing him.

Even if things got complicated, right now she might as well enjoy it while it lasts.

Not everyone can say they've corrupted an Angel.

**Author's Note: Hides behind the Impala, please review!" **


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